2,5-Dichloro-N-(3-methyl-phen-yl)benzenesulfonamide.

In the title compound, C(13)H(11)Cl(2)NO(2)S, the dihedral angle between the aromatic rings is 76.62 (10)° and the C-S-N-C linkage between the rings adopts a gauche conformation [torsion angle = -51.4 (2)°]. A weak intra-molecular C-H⋯O inter-action closes an S(6) ring. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R(2) (2)(8) loops.

Related literature

For related structures, see: Khan et al. (2011 ▶); Mughal et al. (2012 ▶).

Experimental

Crystal data

C13H11Cl2NO2S

M = 316.19

Monoclinic,

a = 9.0361 (10) Å

b = 11.6937 (11) Å

c = 13.6904 (15) Å

β = 100.588 (3)°

V = 1422.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.60 mm−1

T = 296 K

0.41 × 0.32 × 0.26 mm

Data collection

Bruker APEXII CCD diffractometer

4252 measured reflections

2566 independent reflections

2019 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.159

S = 1.06

2566 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812032023/xu5591sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032023/xu5591Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812032023/xu5591Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H11Cl2NO2S	F(000) = 648
Mr = 316.19	Dx = 1.477 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.0361 (10) Å	Cell parameters from 4545 reflections
b = 11.6937 (11) Å	θ = 2.5–27.5°
c = 13.6904 (15) Å	µ = 0.60 mm−1
β = 100.588 (3)°	T = 296 K
V = 1422.0 (3) Å3	Prism, colourless
Z = 4	0.41 × 0.32 × 0.26 mm

Bruker APEXII CCD diffractometer	2019 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
Graphite monochromator	θmax = 25.5°, θmin = 2.3°
ω scans	h = −5→10
4252 measured reflections	k = −13→7
2566 independent reflections	l = −16→16

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.1006P)2 + 0.1252P] where P = (Fo2 + 2Fc2)/3
2566 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.6508 (3)	0.2746 (2)	0.5229 (2)	0.0434 (6)
C2	0.7492 (3)	0.3602 (2)	0.5641 (2)	0.0518 (7)
H2	0.8171	0.3473	0.6229	0.062*
C3	0.7453 (4)	0.4650 (3)	0.5166 (3)	0.0600 (9)
C4	0.6466 (4)	0.4856 (3)	0.4299 (3)	0.0662 (9)
H4	0.6460	0.5562	0.3985	0.079*
C5	0.5481 (4)	0.4010 (3)	0.3895 (3)	0.0614 (8)
H5	0.4805	0.4145	0.3308	0.074*
C6	0.5494 (3)	0.2971 (2)	0.4355 (2)	0.0455 (7)
C7	0.4253 (3)	0.1890 (2)	0.66797 (19)	0.0412 (6)
C8	0.2706 (3)	0.1896 (3)	0.6440 (2)	0.0558 (8)
H8	0.2211	0.1433	0.5930	0.067*
C9	0.1896 (4)	0.2589 (4)	0.6959 (3)	0.0667 (9)
H9	0.0851	0.2590	0.6800	0.080*
C10	0.2613 (4)	0.3283 (3)	0.7712 (3)	0.0585 (8)
H10	0.2053	0.3753	0.8054	0.070*
C11	0.4159 (3)	0.3281 (3)	0.7957 (2)	0.0500 (7)
C12	0.4979 (3)	0.2580 (3)	0.7441 (2)	0.0450 (7)
H12	0.6025	0.2573	0.7606	0.054*
C13	0.4965 (4)	0.4020 (4)	0.8794 (3)	0.0768 (11)
H13A	0.6001	0.3789	0.8961	0.115*
H13B	0.4496	0.3934	0.9364	0.115*
H13C	0.4912	0.4806	0.8588	0.115*
S1	0.66516 (7)	0.13999 (6)	0.58357 (5)	0.0423 (3)
N1	0.5049 (3)	0.1135 (2)	0.61442 (17)	0.0453 (6)
H1	0.4508	0.0653	0.5765	0.054*
O1	0.6848 (2)	0.05302 (16)	0.51318 (15)	0.0499 (5)
O2	0.7776 (2)	0.15261 (18)	0.67029 (16)	0.0548 (6)
Cl1	0.42138 (9)	0.19405 (7)	0.38259 (6)	0.0597 (3)
Cl2	0.86761 (14)	0.57071 (9)	0.57067 (10)	0.0941 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0399 (15)	0.0476 (15)	0.0414 (15)	0.0030 (12)	0.0040 (12)	−0.0048 (12)
C2	0.0420 (16)	0.0568 (18)	0.0538 (19)	−0.0010 (13)	0.0014 (13)	−0.0093 (14)
C3	0.0599 (19)	0.0472 (18)	0.076 (2)	−0.0077 (14)	0.0209 (18)	−0.0136 (16)
C4	0.087 (2)	0.0502 (19)	0.065 (2)	0.0030 (17)	0.024 (2)	0.0066 (16)
C5	0.070 (2)	0.061 (2)	0.0507 (19)	0.0029 (16)	0.0039 (16)	0.0112 (15)
C6	0.0462 (16)	0.0493 (16)	0.0382 (15)	0.0026 (12)	0.0006 (12)	−0.0016 (12)
C7	0.0460 (15)	0.0441 (15)	0.0312 (14)	−0.0006 (11)	0.0012 (11)	0.0037 (11)
C8	0.0439 (17)	0.071 (2)	0.0488 (18)	−0.0107 (14)	−0.0007 (14)	−0.0142 (15)
C9	0.0389 (17)	0.093 (3)	0.066 (2)	−0.0041 (16)	0.0035 (15)	−0.0102 (19)
C10	0.0505 (18)	0.069 (2)	0.058 (2)	0.0003 (15)	0.0148 (16)	−0.0098 (16)
C11	0.0496 (17)	0.0591 (18)	0.0402 (16)	−0.0040 (13)	0.0053 (13)	−0.0038 (13)
C12	0.0409 (15)	0.0536 (17)	0.0368 (14)	−0.0033 (12)	−0.0024 (12)	−0.0035 (12)
C13	0.070 (2)	0.085 (3)	0.072 (2)	−0.0048 (19)	0.0063 (19)	−0.038 (2)
S1	0.0405 (4)	0.0450 (4)	0.0364 (4)	0.0049 (3)	−0.0060 (3)	−0.0037 (3)
N1	0.0494 (14)	0.0462 (13)	0.0369 (13)	−0.0051 (10)	−0.0008 (10)	−0.0077 (10)
O1	0.0494 (11)	0.0508 (12)	0.0460 (11)	0.0072 (9)	0.0000 (9)	−0.0093 (9)
O2	0.0464 (12)	0.0668 (14)	0.0420 (12)	0.0069 (9)	−0.0158 (9)	−0.0045 (9)
Cl1	0.0523 (5)	0.0712 (6)	0.0468 (5)	−0.0060 (4)	−0.0143 (3)	0.0039 (3)
Cl2	0.1001 (8)	0.0623 (6)	0.1198 (10)	−0.0296 (5)	0.0204 (7)	−0.0255 (6)

C1—C2	1.388 (4)	C8—H8	0.9300
C1—C6	1.392 (4)	C9—C10	1.376 (5)
C1—S1	1.773 (3)	C9—H9	0.9300
C2—C3	1.385 (4)	C10—C11	1.375 (5)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.369 (5)	C11—C12	1.384 (4)
C3—Cl2	1.732 (3)	C11—C13	1.510 (4)
C4—C5	1.377 (5)	C12—H12	0.9300
C4—H4	0.9300	C13—H13A	0.9600
C5—C6	1.367 (4)	C13—H13B	0.9600
C5—H5	0.9300	C13—H13C	0.9600
C6—Cl1	1.734 (3)	S1—O2	1.421 (2)
C7—C8	1.376 (4)	S1—O1	1.434 (2)
C7—C12	1.384 (4)	S1—N1	1.611 (3)
C7—N1	1.425 (4)	N1—H1	0.8562
C8—C9	1.374 (5)
C2—C1—C6	119.0 (3)	C10—C9—H9	119.6
C2—C1—S1	117.6 (2)	C11—C10—C9	120.0 (3)
C6—C1—S1	123.4 (2)	C11—C10—H10	120.0
C3—C2—C1	119.2 (3)	C9—C10—H10	120.0
C3—C2—H2	120.4	C10—C11—C12	119.4 (3)
C1—C2—H2	120.4	C10—C11—C13	120.8 (3)
C4—C3—C2	121.3 (3)	C12—C11—C13	119.8 (3)
C4—C3—Cl2	120.5 (3)	C11—C12—C7	120.3 (3)
C2—C3—Cl2	118.1 (3)	C11—C12—H12	119.8
C3—C4—C5	119.4 (3)	C7—C12—H12	119.8
C3—C4—H4	120.3	C11—C13—H13A	109.5
C5—C4—H4	120.3	C11—C13—H13B	109.5
C6—C5—C4	120.3 (3)	H13A—C13—H13B	109.5
C6—C5—H5	119.9	C11—C13—H13C	109.5
C4—C5—H5	119.9	H13A—C13—H13C	109.5
C5—C6—C1	120.8 (3)	H13B—C13—H13C	109.5
C5—C6—Cl1	118.5 (2)	O2—S1—O1	118.51 (12)
C1—C6—Cl1	120.7 (2)	O2—S1—N1	109.86 (13)
C8—C7—C12	119.8 (3)	O1—S1—N1	105.52 (12)
C8—C7—N1	117.9 (3)	O2—S1—C1	106.17 (13)
C12—C7—N1	122.3 (3)	O1—S1—C1	108.81 (13)
C9—C8—C7	119.5 (3)	N1—S1—C1	107.55 (13)
C9—C8—H8	120.2	C7—N1—S1	125.4 (2)
C7—C8—H8	120.2	C7—N1—H1	115.7
C8—C9—C10	120.9 (3)	S1—N1—H1	114.1
C8—C9—H9	119.6
C6—C1—C2—C3	−0.7 (4)	C9—C10—C11—C12	0.1 (5)
S1—C1—C2—C3	177.4 (2)	C9—C10—C11—C13	−178.8 (4)
C1—C2—C3—C4	−0.1 (5)	C10—C11—C12—C7	0.3 (5)
C1—C2—C3—Cl2	179.1 (2)	C13—C11—C12—C7	179.3 (3)
C2—C3—C4—C5	0.6 (5)	C8—C7—C12—C11	−0.4 (4)
Cl2—C3—C4—C5	−178.6 (3)	N1—C7—C12—C11	−178.4 (3)
C3—C4—C5—C6	−0.2 (5)	C2—C1—S1—O2	3.2 (3)
C4—C5—C6—C1	−0.6 (5)	C6—C1—S1—O2	−178.7 (2)
C4—C5—C6—Cl1	179.1 (3)	C2—C1—S1—O1	−125.3 (2)
C2—C1—C6—C5	1.1 (4)	C6—C1—S1—O1	52.7 (3)
S1—C1—C6—C5	−176.9 (2)	C2—C1—S1—N1	120.8 (2)
C2—C1—C6—Cl1	−178.6 (2)	C6—C1—S1—N1	−61.1 (3)
S1—C1—C6—Cl1	3.4 (4)	C8—C7—N1—S1	144.7 (2)
C12—C7—C8—C9	0.1 (5)	C12—C7—N1—S1	−37.2 (4)
N1—C7—C8—C9	178.2 (3)	O2—S1—N1—C7	63.7 (2)
C7—C8—C9—C10	0.4 (6)	O1—S1—N1—C7	−167.5 (2)
C8—C9—C10—C11	−0.5 (6)	C1—S1—N1—C7	−51.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.09	2.946 (3)	178
C12—H12···O2	0.93	2.50	3.141 (3)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.09	2.946 (3)	178
C12—H12⋯O2	0.93	2.50	3.141 (3)	126

Symmetry code: (i) .